Glyoxylic Acid → HCID 10587069, compound

HRID 411644Notes

Reaction equation

HRID 411644 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](O)(=O)C=O.C([O-])([O-])=O.[K+].[K+].[N+:21]([CH:23]([C:34]1[CH:38]=[CH:37][S:36][CH:35]=1)S(C1C=CC(C)=CC=1)(=O)=O)#[C-:22]>CN(C=O)C.[Cl-].[Na+].O>[C:1]1([C@H:7]([N:9]2[CH:10]=[C:23]([C:34]3[CH:38]=[CH:37][S:36][CH:35]=3)[N:21]=[CH:22]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 760Glyoxylic AcidHCID 11430Potassium CarbonateHCID 6431891-Phenethylamine, (+)-HCID 11022211HCID 11022211, compound

Product 1

HCID 10587069HCID 10587069, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(R)-1-Phenyl-ethylamine (1.5 equivalents), glyoxylic acid (1.3 equivalents) and K2CO3 (2.5 equivalents) are combined in DMF. After 3h, add the 3-[1-isocyano-1-(toluene-4-sulfonyl)-methyl]-thiophene (1 equivalent) and stir the reaction at RT for 18 h. Pour the reaction mixture into brine and extract with Et2O. Dry the combined organic extracts over K2CO3 and isolate the desired product by flash chromatography.

Workup

  1. customthe reaction at RT for 18 h
  2. extractionextract with Et2O
  3. dry with materialDry the combined organic extracts over K2CO3

Sources & evidence

ORD record
ord-eb83ca272c6545e98d97bcbf822be511
Source dataset
uspto-grants-2003_05
Patent number
US06559172B1

Reaction notes

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